Adenine → 9-Methyladenine

HRID 1901234Notes

Reaction equation

HRID 1901234 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[OH-].[CH2:12]([N+](CCCC)(CCCC)CCCC)CCC.CI.O>C(Cl)Cl.CO>[CH3:12][N:5]1[CH:6]=[N:7][C:8]2[C:4]1=[N:3][CH:2]=[N:1][C:9]=2[NH2:10]

Participants

7

Reactant 4

HCID 190AdenineHCID 962WaterHCID 6328Methyl iodideHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 696899-Methyladenine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent4×

Procedure

A mixture of 43.2 g (0.23 mol) of adenine and 210 ml of 40% aqueous tetrabutylammonium hydroxide was stirred at room temperature for 30 minutes and 250 ml of methylene chloride was added. To this heterogenous mixture was added 40 ml (0.64 mol) of methyl iodide in 200 ml of methylene chloride. A further 450 ml of methylene chloride was added and the reaction was stirred vigorously for ten hours. The reaction was cooled to 10° and the liquid phase comprising methylene chloride and water was decanted from a milky precipitate which had formed. Methanol was added to the precipitate and the mixture warmed gently to 40°, cooled to 10° and the resulting granular solid filtered off. The solid was recrystallized from 350 ml of water to provide 20.9 g of 9-methyladenine.

Workup

  1. stirringthe reaction was stirred vigorously for ten hours
  2. temperatureThe reaction was cooled to 10°
  3. customwas decanted from a milky precipitate which
  4. customhad formed
  5. temperaturethe mixture warmed gently to 40°
  6. temperaturecooled to 10°
  7. filtrationthe resulting granular solid filtered off
  8. customThe solid was recrystallized from 350 ml of water

Sources & evidence

ORD record
ord-550e2621c1f34c7fb07116b3daef5f3e
Source dataset
uspto-grants-1996_11
Patent number
US05576427

Reaction notes

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